BETA-CYCLODEXTRIN CHIRAL STATIONARY PHASES FOR LIQUID-CHROMATOGRAPHY - EFFECT OF THE SPACER ARM ON CHIRAL RECOGNITION

Cyclodextrins (CDs) can be bound on silica to prepare chiral stationary phases (CSPs) for liquid chromatography. The cyclodextrin ring is connected to a spacer previously bonded on the silica surface. Three different CD-CSPs were prepared with three different spacers. (i) A dimethylethoxysilane with a linear 6 carbon chain produced a monomeric layer. The bonded CD units can move and rotate freely. (ii) The corresponding trimethoxysilane produced a polymeric layer. The bonded CD units were not located at the same distance of the silica surface, but they could still move and rotate freely. (iii) The third spacer contained a cyclohexyl ring that may introduce some conformational rigidity in the CD connection to silica. The three CSPs prepared contained a CD surface coverage of about 0.3 mumol/m2 which is approximately half of the maximum theoretical CD coverage. The first spacer was the most efficient to bond CDs with an average value of 1.7 spacers per CD ring, whereas 5.5 spacers per CD ring were needed with the two other spacers. The chiral recognition capabilities of the three phases were compared using 14 racemic compounds. No pronounced differences were noted, but the CSP prepared with the dimethylethoxysilane monomeric spacer seems to be the most efficient for chiral recognition.